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Supramolecular Daisy Chains

Cantrill, Stuart J. and Youn, Gilmer J. and Stoddart, J. Fraser and Williams, David J. (2001) Supramolecular Daisy Chains. Journal of Organic Chemistry, 66 (21). pp. 6857-6872. ISSN 0022-3263.

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Two series of self-complementary daisy chain monomers, in which a secondary ammonium ion-containing arm is grafted onto a macrocycle with either a [24]- or [25]crown-8 constitution, have been synthesized. In the solid- and ‘gas'-phases, the parent [24]crown-8-based monomer forms dimeric superstructures, as revealed by X-ray crystallography and mass spectrometry, respectively. Elucidation of the complicated solution-phase behavior of this compound was facilitated by the synthesis and study of both deuterated, and fluorinated, analogues. These investigations revealed that the cyclic dimeric superstructure also dominates in solution, except when extremes of either concentration (low), temperature (high), or solvent polarity (highly polar, e.g., dimethyl sulfoxide) are employed. Whereas, upon aggregation, the [24]crown-8-based daisy chain monomers have the capacity to form stereoisomeric superstructures further complicating the study of this series of compounds. The assembly of [25]crown-8-based monomers gives only achiral superstructures. The weaker association exhibited between secondary dialkylammonium ions and crown ethers with a [25]crown-8 constitution, however, resulted in limited oligomerization only dimeric and trimeric superstructures were formed at experimentally attainable concentrations of [25]crown-8-based daisy chain monomers.

Item Type:Article
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Cantrill, Stuart J.0000-0002-3754-7902
Stoddart, J. Fraser0000-0003-3161-3697
Additional Information:© 2001 American Chemical Society. Received 19 April 2001. Published online 26 September 2001. Published in print 1 October 2001. This research was supported by the National Science Foundation. Anthony Pease is thanked for producing the ray-traced pictures contained within this paper.
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Issue or Number:21
Record Number:CaltechAUTHORS:20170426-144501570
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Official Citation:Supramolecular Daisy Chains Stuart J. Cantrill, Gilmer J. Youn, J. Fraser Stoddart, and David J. Williams The Journal of Organic Chemistry 2001 66 (21), 6857-6872 DOI: 10.1021/jo010405h
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76959
Deposited By: Ruth Sustaita
Deposited On:26 Apr 2017 23:02
Last Modified:03 Oct 2019 17:51

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